# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Axel Jacobi von Wangelin' _publ_contact_author_email AXEL.JACOBI@UNI-KOELN.DE _publ_section_title ; On New N-Heterocyclic Carbene Derived Alkylidene Imidazolines ; loop_ _publ_author_name 'A.J.von Wangelin' 'Christiane E. I. Knappke' 'Jorg M. Neudorfl' # Attachment '3.cif' data_zz2 _database_code_depnum_ccdc_archive 'CCDC 751976' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H45 N2, I' _chemical_formula_sum 'C35 H45 I N2' _chemical_formula_weight 620.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9198(3) _cell_length_b 10.5205(4) _cell_length_c 16.6770(6) _cell_angle_alpha 83.068(2) _cell_angle_beta 85.616(2) _cell_angle_gamma 69.015(2) _cell_volume 1612.08(10) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 11853 _cell_measurement_theta_min 1.23 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11853 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7035 _reflns_number_gt 5960 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7035 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.32090(17) -0.01333(17) 0.82429(10) 0.0169(4) Uani 1 1 d . . . N3 N 0.31140(16) 0.06388(17) 0.69760(10) 0.0155(4) Uani 1 1 d . . . C2 C 0.2305(2) 0.0432(2) 0.76286(12) 0.0149(4) Uani 1 1 d . . . C4 C 0.4554(2) 0.0173(2) 0.71829(13) 0.0214(5) Uani 1 1 d . . . H4 H 0.5349 0.0191 0.6833 0.026 Uiso 1 1 calc R . . C5 C 0.4615(2) -0.0304(2) 0.79634(13) 0.0226(5) Uani 1 1 d . . . H5 H 0.5461 -0.0689 0.8271 0.027 Uiso 1 1 calc R . . C6 C 0.2813(2) -0.0508(2) 0.90697(12) 0.0180(5) Uani 1 1 d . . . C6A C 0.2590(2) 0.1307(2) 0.61900(12) 0.0162(4) Uani 1 1 d . . . C7 C 0.2431(2) 0.0490(2) 0.96098(12) 0.0192(5) Uani 1 1 d . . . C7A C 0.2253(2) 0.2726(2) 0.60565(13) 0.0192(5) Uani 1 1 d . . . C8 C 0.2128(2) 0.0082(2) 1.04084(13) 0.0249(5) Uani 1 1 d . . . H8 H 0.1844 0.0732 1.0795 0.030 Uiso 1 1 calc R . . C8A C 0.1752(2) 0.3341(2) 0.53006(13) 0.0254(5) Uani 1 1 d . . . H8B H 0.1501 0.4303 0.5186 0.030 Uiso 1 1 calc R . . C9 C 0.2235(2) -0.1258(2) 1.06461(13) 0.0266(5) Uani 1 1 d . . . H9 H 0.2044 -0.1519 1.1196 0.032 Uiso 1 1 calc R . . C9A C 0.1609(2) 0.2586(3) 0.47105(14) 0.0285(6) Uani 1 1 d . . . H9B H 0.1260 0.3034 0.4198 0.034 Uiso 1 1 calc R . . C10 C 0.2616(2) -0.2213(2) 1.00966(13) 0.0244(5) Uani 1 1 d . . . H10 H 0.2677 -0.3125 1.0272 0.029 Uiso 1 1 calc R . . C10A C 0.1970(2) 0.1188(2) 0.48593(13) 0.0234(5) Uani 1 1 d . . . H10B H 0.1870 0.0682 0.4447 0.028 Uiso 1 1 calc R . . C11 C 0.2912(2) -0.1867(2) 0.92867(13) 0.0195(5) Uani 1 1 d . . . C11A C 0.2478(2) 0.0507(2) 0.56041(12) 0.0181(5) Uani 1 1 d . . . C12 C 0.3376(2) -0.2943(2) 0.86935(13) 0.0261(5) Uani 1 1 d . . . H12 H 0.3319 -0.2460 0.8136 0.031 Uiso 1 1 calc R . . C12A C 0.2923(2) -0.1042(2) 0.57379(13) 0.0232(5) Uani 1 1 d . . . H12B H 0.3304 -0.1357 0.6293 0.028 Uiso 1 1 calc R . . C13 C 0.4952(2) -0.3878(3) 0.88214(16) 0.0388(6) Uani 1 1 d . . . H13A H 0.5579 -0.3331 0.8729 0.058 Uiso 1 1 calc R . . H13B H 0.5235 -0.4577 0.8441 0.058 Uiso 1 1 calc R . . H13C H 0.5049 -0.4322 0.9376 0.058 Uiso 1 1 calc R . . C13A C 0.4119(2) -0.1703(3) 0.51216(15) 0.0339(6) Uani 1 1 d . . . H13D H 0.3773 -0.1368 0.4574 0.051 Uiso 1 1 calc R . . H13E H 0.4381 -0.2699 0.5202 0.051 Uiso 1 1 calc R . . H13F H 0.4967 -0.1464 0.5194 0.051 Uiso 1 1 calc R . . C14 C 0.2396(3) -0.3784(3) 0.87499(17) 0.0389(7) Uani 1 1 d . . . H14A H 0.2440 -0.4276 0.9291 0.058 Uiso 1 1 calc R . . H14B H 0.2717 -0.4443 0.8345 0.058 Uiso 1 1 calc R . . H14C H 0.1400 -0.3174 0.8650 0.058 Uiso 1 1 calc R . . C14A C 0.1645(3) -0.1500(3) 0.56645(16) 0.0363(6) Uani 1 1 d . . . H14D H 0.0885 -0.1092 0.6066 0.054 Uiso 1 1 calc R . . H14E H 0.1962 -0.2499 0.5760 0.054 Uiso 1 1 calc R . . H14F H 0.1266 -0.1202 0.5121 0.054 Uiso 1 1 calc R . . C15 C 0.2403(2) 0.1938(2) 0.93705(13) 0.0230(5) Uani 1 1 d . . . H15 H 0.2263 0.2146 0.8775 0.028 Uiso 1 1 calc R . . C15A C 0.2459(2) 0.3555(2) 0.66934(14) 0.0239(5) Uani 1 1 d . . . H15B H 0.2378 0.3060 0.7236 0.029 Uiso 1 1 calc R . . C16 C 0.3846(3) 0.2048(3) 0.95433(18) 0.0449(7) Uani 1 1 d . . . H16A H 0.3996 0.1870 1.0126 0.067 Uiso 1 1 calc R . . H16B H 0.3836 0.2970 0.9354 0.067 Uiso 1 1 calc R . . H16C H 0.4630 0.1374 0.9260 0.067 Uiso 1 1 calc R . . C16A C 0.3978(2) 0.3654(3) 0.66025(17) 0.0382(6) Uani 1 1 d . . . H16D H 0.4710 0.2732 0.6655 0.057 Uiso 1 1 calc R . . H16E H 0.4095 0.4174 0.7025 0.057 Uiso 1 1 calc R . . H16F H 0.4094 0.4119 0.6070 0.057 Uiso 1 1 calc R . . C17 C 0.1169(3) 0.3021(3) 0.97989(16) 0.0369(6) Uani 1 1 d . . . H17A H 0.0260 0.2869 0.9753 0.055 Uiso 1 1 calc R . . H17B H 0.1081 0.3936 0.9546 0.055 Uiso 1 1 calc R . . H17C H 0.1379 0.2947 1.0371 0.055 Uiso 1 1 calc R . . C17A C 0.1313(3) 0.4987(2) 0.66742(16) 0.0363(6) Uani 1 1 d . . . H17D H 0.1432 0.5526 0.6170 0.055 Uiso 1 1 calc R . . H17E H 0.1422 0.5434 0.7135 0.055 Uiso 1 1 calc R . . H17F H 0.0350 0.4920 0.6705 0.055 Uiso 1 1 calc R . . C18 C 0.0739(2) 0.0612(2) 0.76770(13) 0.0230(5) Uani 1 1 d . . . H18A H 0.0478 0.0376 0.8246 0.028 Uiso 1 1 calc R . . H18B H 0.0606 -0.0060 0.7353 0.028 Uiso 1 1 calc R . . C19 C -0.0338(2) 0.2033(2) 0.73938(13) 0.0202(5) Uani 1 1 d . . . C20 C -0.0641(2) 0.3114(2) 0.78581(14) 0.0253(5) Uani 1 1 d . . . H20 H -0.0120 0.2994 0.8333 0.030 Uiso 1 1 calc R . . C21 C -0.1692(2) 0.4363(2) 0.76410(14) 0.0278(5) Uani 1 1 d . . . H21 H -0.1879 0.5092 0.7968 0.033 Uiso 1 1 calc R . . C22 C -0.2486(2) 0.4574(2) 0.69467(14) 0.0249(5) Uani 1 1 d . . . C23 C -0.2145(2) 0.3485(3) 0.64786(15) 0.0316(6) Uani 1 1 d . . . H23 H -0.2636 0.3610 0.5992 0.038 Uiso 1 1 calc R . . C24 C -0.1110(2) 0.2228(2) 0.67020(14) 0.0275(5) Uani 1 1 d . . . H24 H -0.0927 0.1493 0.6380 0.033 Uiso 1 1 calc R . . C25 C -0.3643(2) 0.5935(2) 0.67167(16) 0.0370(6) Uani 1 1 d . . . H25A H -0.4576 0.5931 0.6954 0.056 Uiso 1 1 calc R . . H25B H -0.3696 0.6094 0.6127 0.056 Uiso 1 1 calc R . . H25C H -0.3408 0.6664 0.6920 0.056 Uiso 1 1 calc R . . I1 I 0.149551(14) 0.162933(15) 0.248146(8) 0.02378(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0176(9) 0.0221(10) 0.0099(9) 0.0014(7) 0.0004(7) -0.0066(7) N3 0.0164(8) 0.0189(10) 0.0107(9) 0.0000(7) 0.0001(7) -0.0060(7) C2 0.0177(10) 0.0133(11) 0.0138(11) -0.0019(9) -0.0003(8) -0.0055(8) C4 0.0148(10) 0.0285(13) 0.0190(12) -0.0027(10) 0.0031(9) -0.0061(9) C5 0.0145(10) 0.0314(13) 0.0189(12) 0.0019(10) -0.0030(9) -0.0056(9) C6 0.0152(10) 0.0273(13) 0.0104(10) 0.0002(9) 0.0003(8) -0.0069(9) C6A 0.0130(9) 0.0215(12) 0.0136(10) 0.0006(9) 0.0014(8) -0.0068(8) C7 0.0158(10) 0.0248(12) 0.0169(11) -0.0027(9) -0.0001(8) -0.0071(9) C7A 0.0136(10) 0.0216(12) 0.0220(12) -0.0015(9) 0.0030(8) -0.0066(9) C8 0.0243(12) 0.0338(14) 0.0169(12) -0.0086(10) 0.0038(9) -0.0094(10) C8A 0.0225(11) 0.0249(13) 0.0254(13) 0.0071(10) -0.0009(9) -0.0073(10) C9 0.0287(12) 0.0386(15) 0.0135(11) 0.0000(10) 0.0047(9) -0.0152(11) C9A 0.0241(12) 0.0386(15) 0.0199(12) 0.0095(11) -0.0049(9) -0.0108(11) C10 0.0252(12) 0.0274(13) 0.0221(12) 0.0035(10) -0.0010(9) -0.0129(10) C10A 0.0219(11) 0.0348(14) 0.0167(11) -0.0015(10) -0.0006(9) -0.0145(10) C11 0.0178(10) 0.0248(13) 0.0156(11) -0.0002(9) -0.0013(8) -0.0073(9) C11A 0.0158(10) 0.0227(12) 0.0167(11) 0.0004(9) 0.0013(8) -0.0091(9) C12 0.0338(13) 0.0221(13) 0.0193(12) -0.0010(10) -0.0029(10) -0.0062(10) C12A 0.0279(12) 0.0262(13) 0.0179(12) -0.0028(10) 0.0019(9) -0.0127(10) C13 0.0328(14) 0.0390(16) 0.0369(16) -0.0129(13) 0.0046(11) -0.0016(12) C13A 0.0307(13) 0.0314(15) 0.0377(15) -0.0082(12) 0.0064(11) -0.0087(11) C14 0.0390(14) 0.0318(15) 0.0477(17) -0.0144(13) -0.0062(13) -0.0103(12) C14A 0.0452(15) 0.0369(16) 0.0371(15) -0.0118(12) 0.0095(12) -0.0266(12) C15 0.0239(11) 0.0253(13) 0.0201(12) -0.0038(10) -0.0046(9) -0.0078(10) C15A 0.0237(11) 0.0229(13) 0.0260(13) -0.0066(10) 0.0039(9) -0.0091(10) C16 0.0370(15) 0.0328(15) 0.070(2) 0.0030(14) -0.0200(14) -0.0179(12) C16A 0.0315(13) 0.0437(17) 0.0487(17) -0.0240(13) 0.0077(12) -0.0200(12) C17 0.0406(15) 0.0317(15) 0.0357(15) -0.0119(12) -0.0020(12) -0.0065(12) C17A 0.0360(14) 0.0233(14) 0.0463(17) -0.0071(12) 0.0104(12) -0.0076(11) C18 0.0191(11) 0.0272(13) 0.0204(12) 0.0009(10) -0.0001(9) -0.0065(9) C19 0.0183(10) 0.0275(13) 0.0176(11) 0.0003(10) 0.0029(9) -0.0131(9) C20 0.0232(11) 0.0295(14) 0.0227(12) -0.0010(10) -0.0033(9) -0.0086(10) C21 0.0230(12) 0.0306(14) 0.0280(13) -0.0048(11) 0.0021(10) -0.0072(10) C22 0.0180(11) 0.0287(13) 0.0255(13) 0.0036(11) 0.0014(9) -0.0078(10) C23 0.0242(12) 0.0408(15) 0.0281(14) -0.0025(12) -0.0087(10) -0.0083(11) C24 0.0279(12) 0.0290(14) 0.0247(13) -0.0048(11) -0.0036(10) -0.0078(10) C25 0.0266(13) 0.0322(15) 0.0471(17) 0.0056(13) -0.0028(11) -0.0069(11) I1 0.02044(8) 0.03166(10) 0.01984(9) -0.00930(6) 0.00181(6) -0.00828(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.349(2) . ? N1 C5 1.391(3) . ? N1 C6 1.452(2) . ? N3 C2 1.346(2) . ? N3 C4 1.390(2) . ? N3 C6A 1.450(2) . ? C2 C18 1.493(3) . ? C4 C5 1.335(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.396(3) . ? C6 C11 1.401(3) . ? C6A C11A 1.399(3) . ? C6A C7A 1.401(3) . ? C7 C8 1.393(3) . ? C7 C15 1.519(3) . ? C7A C8A 1.387(3) . ? C7A C15A 1.521(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C8A C9A 1.382(3) . ? C8A H8B 0.9500 . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C9A C10A 1.379(3) . ? C9A H9B 0.9500 . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C10A C11A 1.390(3) . ? C10A H10B 0.9500 . ? C11 C12 1.516(3) . ? C11A C12A 1.521(3) . ? C12 C14 1.523(3) . ? C12 C13 1.535(3) . ? C12 H12 1.0000 . ? C12A C14A 1.527(3) . ? C12A C13A 1.530(3) . ? C12A H12B 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C15 C16 1.527(3) . ? C15 C17 1.540(3) . ? C15 H15 1.0000 . ? C15A C17A 1.526(3) . ? C15A C16A 1.542(3) . ? C15A H15B 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17A H17D 0.9800 . ? C17A H17E 0.9800 . ? C17A H17F 0.9800 . ? C18 C19 1.537(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.383(3) . ? C19 C24 1.388(3) . ? C20 C21 1.381(3) . ? C20 H20 0.9500 . ? C21 C22 1.401(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 C25 1.507(3) . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.11(17) . . ? C2 N1 C6 126.59(16) . . ? C5 N1 C6 124.30(16) . . ? C2 N3 C4 109.05(16) . . ? C2 N3 C6A 126.47(16) . . ? C4 N3 C6A 124.40(17) . . ? N3 C2 N1 107.04(16) . . ? N3 C2 C18 128.43(17) . . ? N1 C2 C18 124.15(18) . . ? C5 C4 N3 107.58(18) . . ? C5 C4 H4 126.2 . . ? N3 C4 H4 126.2 . . ? C4 C5 N1 107.21(17) . . ? C4 C5 H5 126.4 . . ? N1 C5 H5 126.4 . . ? C7 C6 C11 124.02(19) . . ? C7 C6 N1 117.86(19) . . ? C11 C6 N1 118.03(18) . . ? C11A C6A C7A 123.67(19) . . ? C11A C6A N3 118.74(18) . . ? C7A C6A N3 117.57(18) . . ? C8 C7 C6 116.6(2) . . ? C8 C7 C15 120.19(19) . . ? C6 C7 C15 123.12(19) . . ? C8A C7A C6A 116.44(19) . . ? C8A C7A C15A 121.2(2) . . ? C6A C7A C15A 122.31(18) . . ? C9 C8 C7 120.9(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C9A C8A C7A 121.5(2) . . ? C9A C8A H8B 119.3 . . ? C7A C8A H8B 119.3 . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C10A C9A C8A 120.5(2) . . ? C10A C9A H9B 119.7 . . ? C8A C9A H9B 119.7 . . ? C9 C10 C11 121.1(2) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C9A C10A C11A 121.0(2) . . ? C9A C10A H10B 119.5 . . ? C11A C10A H10B 119.5 . . ? C10 C11 C6 116.5(2) . . ? C10 C11 C12 120.5(2) . . ? C6 C11 C12 122.96(19) . . ? C10A C11A C6A 116.9(2) . . ? C10A C11A C12A 119.65(19) . . ? C6A C11A C12A 123.40(18) . . ? C11 C12 C14 112.37(19) . . ? C11 C12 C13 110.20(18) . . ? C14 C12 C13 110.6(2) . . ? C11 C12 H12 107.8 . . ? C14 C12 H12 107.8 . . ? C13 C12 H12 107.8 . . ? C11A C12A C14A 111.41(18) . . ? C11A C12A C13A 109.95(18) . . ? C14A C12A C13A 109.34(19) . . ? C11A C12A H12B 108.7 . . ? C14A C12A H12B 108.7 . . ? C13A C12A H12B 108.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12A C14A H14D 109.5 . . ? C12A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C12A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C7 C15 C16 110.30(17) . . ? C7 C15 C17 113.08(19) . . ? C16 C15 C17 109.39(19) . . ? C7 C15 H15 108.0 . . ? C16 C15 H15 108.0 . . ? C17 C15 H15 108.0 . . ? C7A C15A C17A 112.80(18) . . ? C7A C15A C16A 110.80(18) . . ? C17A C15A C16A 109.85(19) . . ? C7A C15A H15B 107.7 . . ? C17A C15A H15B 107.7 . . ? C16A C15A H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C2 C18 C19 117.32(18) . . ? C2 C18 H18A 108.0 . . ? C19 C18 H18A 108.0 . . ? C2 C18 H18B 108.0 . . ? C19 C18 H18B 108.0 . . ? H18A C18 H18B 107.2 . . ? C20 C19 C24 118.7(2) . . ? C20 C19 C18 120.59(19) . . ? C24 C19 C18 120.5(2) . . ? C21 C20 C19 120.9(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.1(2) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 117.2(2) . . ? C23 C22 C25 121.9(2) . . ? C21 C22 C25 120.9(2) . . ? C24 C23 C22 121.8(2) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C19 120.3(2) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 N1 1.0(2) . . . . ? C6A N3 C2 N1 -175.73(18) . . . . ? C4 N3 C2 C18 -172.0(2) . . . . ? C6A N3 C2 C18 11.2(3) . . . . ? C5 N1 C2 N3 -1.1(2) . . . . ? C6 N1 C2 N3 178.67(18) . . . . ? C5 N1 C2 C18 172.4(2) . . . . ? C6 N1 C2 C18 -7.9(3) . . . . ? C2 N3 C4 C5 -0.6(2) . . . . ? C6A N3 C4 C5 176.23(19) . . . . ? N3 C4 C5 N1 -0.1(2) . . . . ? C2 N1 C5 C4 0.7(2) . . . . ? C6 N1 C5 C4 -179.04(19) . . . . ? C2 N1 C6 C7 -87.8(2) . . . . ? C5 N1 C6 C7 91.9(2) . . . . ? C2 N1 C6 C11 95.5(2) . . . . ? C5 N1 C6 C11 -84.8(2) . . . . ? C2 N3 C6A C11A -91.6(2) . . . . ? C4 N3 C6A C11A 92.1(2) . . . . ? C2 N3 C6A C7A 89.8(2) . . . . ? C4 N3 C6A C7A -86.4(2) . . . . ? C11 C6 C7 C8 -0.4(3) . . . . ? N1 C6 C7 C8 -176.79(16) . . . . ? C11 C6 C7 C15 176.82(18) . . . . ? N1 C6 C7 C15 0.4(3) . . . . ? C11A C6A C7A C8A 1.6(3) . . . . ? N3 C6A C7A C8A -179.89(17) . . . . ? C11A C6A C7A C15A -176.84(18) . . . . ? N3 C6A C7A C15A 1.7(3) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C15 C7 C8 C9 -175.99(18) . . . . ? C6A C7A C8A C9A -0.7(3) . . . . ? C15A C7A C8A C9A 177.8(2) . . . . ? C7 C8 C9 C10 -1.3(3) . . . . ? C7A C8A C9A C10A -0.2(3) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C8A C9A C10A C11A 0.3(3) . . . . ? C9 C10 C11 C6 0.5(3) . . . . ? C9 C10 C11 C12 178.05(19) . . . . ? C7 C6 C11 C10 -0.5(3) . . . . ? N1 C6 C11 C10 175.91(17) . . . . ? C7 C6 C11 C12 -177.98(19) . . . . ? N1 C6 C11 C12 -1.6(3) . . . . ? C9A C10A C11A C6A 0.6(3) . . . . ? C9A C10A C11A C12A -177.59(19) . . . . ? C7A C6A C11A C10A -1.6(3) . . . . ? N3 C6A C11A C10A 179.94(18) . . . . ? C7A C6A C11A C12A 176.53(19) . . . . ? N3 C6A C11A C12A -2.0(3) . . . . ? C10 C11 C12 C14 48.8(3) . . . . ? C6 C11 C12 C14 -133.8(2) . . . . ? C10 C11 C12 C13 -75.0(3) . . . . ? C6 C11 C12 C13 102.4(2) . . . . ? C10A C11A C12A C14A -63.0(3) . . . . ? C6A C11A C12A C14A 118.9(2) . . . . ? C10A C11A C12A C13A 58.3(2) . . . . ? C6A C11A C12A C13A -119.7(2) . . . . ? C8 C7 C15 C16 83.8(2) . . . . ? C6 C7 C15 C16 -93.3(2) . . . . ? C8 C7 C15 C17 -39.1(2) . . . . ? C6 C7 C15 C17 143.9(2) . . . . ? C8A C7A C15A C17A 35.8(3) . . . . ? C6A C7A C15A C17A -145.8(2) . . . . ? C8A C7A C15A C16A -87.8(2) . . . . ? C6A C7A C15A C16A 90.6(3) . . . . ? N3 C2 C18 C19 -57.7(3) . . . . ? N1 C2 C18 C19 130.3(2) . . . . ? C2 C18 C19 C20 -73.3(3) . . . . ? C2 C18 C19 C24 112.0(2) . . . . ? C24 C19 C20 C21 0.1(3) . . . . ? C18 C19 C20 C21 -174.7(2) . . . . ? C19 C20 C21 C22 0.3(4) . . . . ? C20 C21 C22 C23 -1.6(3) . . . . ? C20 C21 C22 C25 179.3(2) . . . . ? C21 C22 C23 C24 2.7(4) . . . . ? C25 C22 C23 C24 -178.3(2) . . . . ? C22 C23 C24 C19 -2.4(4) . . . . ? C20 C19 C24 C23 1.0(3) . . . . ? C18 C19 C24 C23 175.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.999 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.069 # Attachment '19.cif' data_19 _database_code_depnum_ccdc_archive 'CCDC 751977' #TrackingRef '19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H49 N2, I' _chemical_formula_sum 'C34 H49 I N2' _chemical_formula_weight 612.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.0042(8) _cell_length_b 18.6505(13) _cell_length_c 20.0765(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6367.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29869 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 27.00 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 1.029 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29869 _diffrn_reflns_av_R_equivalents 0.1138 _diffrn_reflns_av_sigmaI/netI 0.1380 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6958 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1146P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6958 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2076 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2583 _refine_ls_wR_factor_gt 0.2172 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0768(3) 0.4357(4) 0.3297(3) 0.0372(16) Uani 1 1 d . . . N3 N 0.1295(3) 0.4423(3) 0.2310(3) 0.0322(15) Uani 1 1 d . . . C2 C 0.0723(4) 0.4102(4) 0.2674(4) 0.0368(19) Uani 1 1 d . . . C4 C 0.1692(4) 0.4905(4) 0.2725(4) 0.037(2) Uani 1 1 d . . . H4 H 0.2109 0.5212 0.2592 0.045 Uiso 1 1 calc R . . C5 C 0.1396(4) 0.4864(4) 0.3329(4) 0.0346(19) Uani 1 1 d . . . H5 H 0.1566 0.5121 0.3711 0.042 Uiso 1 1 calc R . . C6 C 0.0175(4) 0.4271(4) 0.3832(4) 0.0341(19) Uani 1 1 d . . . C6A C 0.1439(4) 0.4369(5) 0.1596(4) 0.035(2) Uani 1 1 d . . . C7 C -0.0489(4) 0.4674(4) 0.3792(4) 0.0352(19) Uani 1 1 d . . . C7A C 0.1154(4) 0.4937(4) 0.1199(4) 0.038(2) Uani 1 1 d . . . C8 C -0.1017(5) 0.4589(5) 0.4298(4) 0.045(2) Uani 1 1 d . . . H8 H -0.1484 0.4869 0.4297 0.054 Uiso 1 1 calc R . . C8A C 0.1327(4) 0.4888(5) 0.0528(4) 0.047(2) Uani 1 1 d . . . H8B H 0.1170 0.5264 0.0238 0.057 Uiso 1 1 calc R . . C9 C -0.0896(4) 0.4118(4) 0.4805(4) 0.042(2) Uani 1 1 d . . . H9 H -0.1287 0.4065 0.5140 0.051 Uiso 1 1 calc R . . C9A C 0.1727(4) 0.4298(5) 0.0265(4) 0.045(2) Uani 1 1 d . . . H9B H 0.1820 0.4266 -0.0200 0.054 Uiso 1 1 calc R . . C10 C -0.0222(5) 0.3719(4) 0.4842(4) 0.043(2) Uani 1 1 d . . . H10 H -0.0143 0.3402 0.5206 0.051 Uiso 1 1 calc R . . C10A C 0.1980(4) 0.3773(4) 0.0675(4) 0.039(2) Uani 1 1 d . . . H10B H 0.2264 0.3383 0.0488 0.047 Uiso 1 1 calc R . . C11 C 0.0357(4) 0.3777(5) 0.4339(4) 0.040(2) Uani 1 1 d . . . C11A C 0.1846(4) 0.3777(5) 0.1359(4) 0.037(2) Uani 1 1 d . . . C12 C 0.1098(5) 0.3334(4) 0.4365(4) 0.047(2) Uani 1 1 d . . . H12 H 0.1318 0.3299 0.3904 0.057 Uiso 1 1 calc R . . C12A C 0.2130(4) 0.3174(4) 0.1785(4) 0.041(2) Uani 1 1 d . . . H12B H 0.2005 0.3296 0.2258 0.049 Uiso 1 1 calc R . . C13 C 0.0965(6) 0.2584(5) 0.4625(5) 0.071(3) Uani 1 1 d . . . H13A H 0.0810 0.2606 0.5095 0.107 Uiso 1 1 calc R . . H13B H 0.1452 0.2306 0.4583 0.107 Uiso 1 1 calc R . . H13C H 0.0547 0.2352 0.4366 0.107 Uiso 1 1 calc R . . C13A C 0.3028(4) 0.3064(5) 0.1734(4) 0.050(2) Uani 1 1 d . . . H13D H 0.3164 0.2904 0.1283 0.076 Uiso 1 1 calc R . . H13E H 0.3194 0.2700 0.2057 0.076 Uiso 1 1 calc R . . H13F H 0.3297 0.3517 0.1830 0.076 Uiso 1 1 calc R . . C14 C 0.1713(5) 0.3720(5) 0.4816(4) 0.060(3) Uani 1 1 d . . . H14A H 0.1774 0.4218 0.4668 0.090 Uiso 1 1 calc R . . H14B H 0.2220 0.3473 0.4783 0.090 Uiso 1 1 calc R . . H14C H 0.1531 0.3713 0.5279 0.090 Uiso 1 1 calc R . . C14A C 0.1725(5) 0.2470(4) 0.1625(4) 0.055(3) Uani 1 1 d . . . H14D H 0.1154 0.2538 0.1637 0.082 Uiso 1 1 calc R . . H14E H 0.1877 0.2108 0.1954 0.082 Uiso 1 1 calc R . . H14F H 0.1883 0.2310 0.1179 0.082 Uiso 1 1 calc R . . C15 C -0.0607(4) 0.5227(5) 0.3219(4) 0.046(2) Uani 1 1 d . . . H15 H -0.0317 0.5054 0.2817 0.056 Uiso 1 1 calc R . . C15A C 0.0697(4) 0.5577(4) 0.1468(4) 0.041(2) Uani 1 1 d . . . H15B H 0.0564 0.5474 0.1944 0.049 Uiso 1 1 calc R . . C16 C -0.0299(5) 0.5962(4) 0.3405(4) 0.047(2) Uani 1 1 d . . . H16A H -0.0551 0.6123 0.3817 0.070 Uiso 1 1 calc R . . H16B H -0.0417 0.6302 0.3046 0.070 Uiso 1 1 calc R . . H16C H 0.0272 0.5937 0.3471 0.070 Uiso 1 1 calc R . . C16A C -0.0070(5) 0.5699(5) 0.1097(5) 0.059(3) Uani 1 1 d . . . H16D H 0.0044 0.5836 0.0636 0.088 Uiso 1 1 calc R . . H16E H -0.0367 0.6083 0.1315 0.088 Uiso 1 1 calc R . . H16F H -0.0381 0.5257 0.1101 0.088 Uiso 1 1 calc R . . C17 C -0.1502(4) 0.5292(5) 0.3041(5) 0.071(3) Uani 1 1 d . . . H17A H -0.1711 0.4817 0.2930 0.107 Uiso 1 1 calc R . . H17B H -0.1566 0.5612 0.2658 0.107 Uiso 1 1 calc R . . H17C H -0.1789 0.5487 0.3423 0.107 Uiso 1 1 calc R . . C17A C 0.1210(5) 0.6246(5) 0.1455(5) 0.063(3) Uani 1 1 d . . . H17D H 0.1680 0.6167 0.1728 0.094 Uiso 1 1 calc R . . H17E H 0.0912 0.6653 0.1633 0.094 Uiso 1 1 calc R . . H17F H 0.1367 0.6349 0.0995 0.094 Uiso 1 1 calc R . . C18 C 0.0173(4) 0.3527(4) 0.2431(4) 0.039(2) Uani 1 1 d . . . C19 C -0.0264(5) 0.3706(5) 0.1913(5) 0.049(2) Uani 1 1 d . . . H19 H -0.0210 0.4193 0.1782 0.058 Uiso 1 1 calc R . . C20 C -0.0826(5) 0.3291(7) 0.1496(5) 0.075(3) Uani 1 1 d . . . C21 C -0.0529(6) 0.3319(8) 0.0784(6) 0.109(5) Uani 1 1 d . . . H21A H -0.0009 0.3094 0.0759 0.164 Uiso 1 1 calc R . . H21B H -0.0490 0.3820 0.0640 0.164 Uiso 1 1 calc R . . H21C H -0.0895 0.3061 0.0492 0.164 Uiso 1 1 calc R . . C22 C -0.0861(4) 0.2578(4) 0.1734(5) 0.050(3) Uani 1 1 d . . . H22A H -0.1312 0.2333 0.1533 0.061 Uiso 0.50 1 d PR . . H22B H -0.0918 0.2582 0.2219 0.061 Uiso 0.50 1 d PR . . H22C H -0.0376 0.2325 0.1613 0.061 Uiso 0.50 1 d PR . . H22D H -0.0425 0.2494 0.2044 0.061 Uiso 0.50 1 d PR . . H22E H -0.0819 0.2245 0.1358 0.061 Uiso 0.50 1 d PR . . H22F H -0.1362 0.2501 0.1964 0.061 Uiso 0.50 1 d PR . . C23 C -0.1644(4) 0.3671(6) 0.1514(4) 0.062(3) Uani 1 1 d . . . H23A H -0.2016 0.3406 0.1233 0.094 Uiso 1 1 calc R . . H23B H -0.1590 0.4162 0.1347 0.094 Uiso 1 1 calc R . . H23C H -0.1839 0.3682 0.1973 0.094 Uiso 1 1 calc R . . C24 C 0.0179(5) 0.2849(4) 0.2830(4) 0.052(2) Uani 1 1 d . . . H24A H 0.0384 0.2948 0.3277 0.062 Uiso 0.50 1 d PR . . H24B H 0.0516 0.2494 0.2610 0.062 Uiso 0.50 1 d PR . . H24C H -0.0357 0.2661 0.2864 0.062 Uiso 0.50 1 d PR . . H24D H -0.0022 0.2454 0.2557 0.062 Uiso 0.50 1 d PR . . H24E H -0.0154 0.2908 0.3224 0.062 Uiso 0.50 1 d PR . . H24F H 0.0719 0.2741 0.2970 0.062 Uiso 0.50 1 d PR . . I1 I 0.24961(3) 0.15598(3) 0.35284(3) 0.0587(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.038(4) 0.043(4) 0.031(4) 0.000(3) 0.000(3) 0.004(3) N3 0.030(3) 0.038(4) 0.029(4) -0.001(3) 0.005(3) -0.005(3) C2 0.032(4) 0.041(5) 0.037(5) 0.000(4) -0.001(4) 0.009(4) C4 0.038(4) 0.036(5) 0.038(5) -0.006(4) 0.000(4) 0.001(4) C5 0.021(4) 0.036(5) 0.047(6) -0.009(4) -0.005(4) 0.001(3) C6 0.033(4) 0.040(5) 0.030(5) -0.002(4) 0.004(4) -0.001(4) C6A 0.022(4) 0.045(5) 0.039(5) -0.002(4) 0.000(3) -0.007(4) C7 0.029(4) 0.037(5) 0.039(5) -0.008(4) -0.004(4) 0.000(4) C7A 0.035(4) 0.035(5) 0.044(6) -0.008(4) 0.000(4) -0.004(4) C8 0.045(5) 0.045(6) 0.045(6) -0.009(5) -0.008(4) 0.006(4) C8A 0.044(5) 0.050(6) 0.049(6) 0.002(5) -0.011(4) 0.002(4) C9 0.037(5) 0.050(6) 0.039(5) -0.014(5) 0.007(4) -0.007(4) C9A 0.043(5) 0.065(6) 0.027(5) 0.003(5) 0.004(4) -0.007(5) C10 0.058(5) 0.038(5) 0.032(5) -0.001(4) 0.005(4) 0.006(4) C10A 0.035(5) 0.041(5) 0.042(6) -0.014(4) 0.006(4) -0.005(4) C11 0.037(5) 0.049(5) 0.033(5) -0.011(4) 0.003(4) 0.001(4) C11A 0.034(4) 0.036(5) 0.043(6) -0.004(4) -0.004(4) -0.011(4) C12 0.058(5) 0.053(6) 0.030(5) 0.003(4) 0.013(4) 0.031(5) C12A 0.037(4) 0.039(5) 0.047(6) -0.008(4) 0.004(4) 0.002(4) C13 0.097(7) 0.050(6) 0.066(7) 0.007(6) -0.006(6) 0.030(5) C13A 0.056(6) 0.045(6) 0.050(6) -0.007(5) -0.007(4) -0.005(4) C14 0.051(5) 0.091(7) 0.038(6) 0.006(5) 0.001(4) 0.024(5) C14A 0.071(6) 0.033(5) 0.061(7) -0.011(5) -0.011(5) -0.001(5) C15 0.037(5) 0.052(6) 0.050(6) -0.005(5) -0.006(4) 0.016(4) C15A 0.035(4) 0.040(5) 0.048(5) -0.002(4) -0.005(4) 0.008(4) C16 0.041(5) 0.042(5) 0.057(7) -0.001(5) -0.006(4) -0.008(4) C16A 0.063(6) 0.050(6) 0.064(7) -0.001(5) -0.004(5) 0.011(5) C17 0.055(6) 0.054(7) 0.105(9) 0.005(6) -0.035(6) 0.005(5) C17A 0.062(6) 0.046(6) 0.080(8) -0.003(5) 0.014(5) 0.012(5) C18 0.034(5) 0.045(5) 0.037(5) -0.004(4) -0.001(4) -0.001(4) C19 0.042(5) 0.058(6) 0.045(6) 0.001(5) 0.003(5) -0.008(4) C20 0.041(6) 0.114(10) 0.070(8) -0.017(7) 0.003(5) 0.007(6) C21 0.085(8) 0.175(14) 0.067(9) -0.047(9) -0.001(6) 0.008(8) C22 0.035(5) 0.019(4) 0.097(8) 0.003(5) -0.043(5) 0.000(4) C23 0.035(5) 0.087(8) 0.065(7) -0.001(6) -0.011(4) 0.000(5) C24 0.068(6) 0.039(6) 0.048(6) 0.000(5) 0.014(5) -0.009(4) I1 0.0628(5) 0.0525(4) 0.0608(5) -0.0054(3) 0.0097(3) 0.0080(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.341(9) . ? N1 C5 1.427(9) . ? N1 C6 1.482(9) . ? N3 C2 1.355(9) . ? N3 C4 1.399(9) . ? N3 C6A 1.459(9) . ? C2 C18 1.504(10) . ? C4 C5 1.315(10) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.360(10) . ? C6 C11 1.406(11) . ? C6A C11A 1.386(11) . ? C6A C7A 1.412(11) . ? C7 C8 1.365(11) . ? C7 C15 1.558(11) . ? C7A C8A 1.383(11) . ? C7A C15A 1.523(10) . ? C8 C9 1.360(11) . ? C8 H8 0.9500 . ? C8A C9A 1.397(11) . ? C8A H8B 0.9500 . ? C9 C10 1.369(10) . ? C9 H9 0.9500 . ? C9A C10A 1.349(11) . ? C9A H9B 0.9500 . ? C10 C11 1.414(10) . ? C10 H10 0.9500 . ? C10A C11A 1.393(10) . ? C10A H10B 0.9500 . ? C11 C12 1.509(10) . ? C11A C12A 1.493(11) . ? C12 C13 1.510(11) . ? C12 C14 1.559(11) . ? C12 H12 1.0000 . ? C12A C14A 1.516(11) . ? C12A C13A 1.545(10) . ? C12A H12B 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C15 C16 1.515(11) . ? C15 C17 1.568(10) . ? C15 H15 1.0000 . ? C15A C16A 1.519(11) . ? C15A C17A 1.523(12) . ? C15A H15B 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17A H17D 0.9800 . ? C17A H17E 0.9800 . ? C17A H17F 0.9800 . ? C18 C19 1.321(10) . ? C18 C24 1.497(11) . ? C19 C20 1.487(13) . ? C19 H19 0.9500 . ? C20 C22 1.414(13) . ? C20 C21 1.517(13) . ? C20 C23 1.562(12) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9801 . ? C22 H22C 0.9801 . ? C22 H22D 0.9802 . ? C22 H22E 0.9799 . ? C22 H22F 0.9799 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9798 . ? C24 H24B 0.9801 . ? C24 H24C 0.9801 . ? C24 H24D 0.9801 . ? C24 H24E 0.9800 . ? C24 H24F 0.9801 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 108.6(6) . . ? C2 N1 C6 126.8(6) . . ? C5 N1 C6 123.3(7) . . ? C2 N3 C4 108.0(6) . . ? C2 N3 C6A 128.3(6) . . ? C4 N3 C6A 123.3(6) . . ? N1 C2 N3 107.8(7) . . ? N1 C2 C18 126.2(7) . . ? N3 C2 C18 125.9(7) . . ? C5 C4 N3 109.0(7) . . ? C5 C4 H4 125.5 . . ? N3 C4 H4 125.5 . . ? C4 C5 N1 106.5(7) . . ? C4 C5 H5 126.7 . . ? N1 C5 H5 126.7 . . ? C7 C6 C11 126.0(7) . . ? C7 C6 N1 117.6(7) . . ? C11 C6 N1 116.5(6) . . ? C11A C6A C7A 125.2(8) . . ? C11A C6A N3 118.4(7) . . ? C7A C6A N3 116.4(7) . . ? C6 C7 C8 116.0(8) . . ? C6 C7 C15 121.1(7) . . ? C8 C7 C15 122.8(7) . . ? C8A C7A C6A 115.3(7) . . ? C8A C7A C15A 120.4(8) . . ? C6A C7A C15A 124.3(8) . . ? C9 C8 C7 122.2(8) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C7A C8A C9A 121.5(8) . . ? C7A C8A H8B 119.2 . . ? C9A C8A H8B 119.2 . . ? C8 C9 C10 121.1(8) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C10A C9A C8A 119.8(8) . . ? C10A C9A H9B 120.1 . . ? C8A C9A H9B 120.1 . . ? C9 C10 C11 120.2(8) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C9A C10A C11A 123.0(8) . . ? C9A C10A H10B 118.5 . . ? C11A C10A H10B 118.5 . . ? C6 C11 C10 114.5(7) . . ? C6 C11 C12 124.6(7) . . ? C10 C11 C12 121.0(8) . . ? C6A C11A C10A 115.1(8) . . ? C6A C11A C12A 124.4(8) . . ? C10A C11A C12A 120.5(8) . . ? C11 C12 C13 113.2(7) . . ? C11 C12 C14 109.1(7) . . ? C13 C12 C14 109.2(7) . . ? C11 C12 H12 108.4 . . ? C13 C12 H12 108.4 . . ? C14 C12 H12 108.4 . . ? C11A C12A C14A 112.5(7) . . ? C11A C12A C13A 112.5(7) . . ? C14A C12A C13A 108.6(7) . . ? C11A C12A H12B 107.7 . . ? C14A C12A H12B 107.7 . . ? C13A C12A H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12A C14A H14D 109.5 . . ? C12A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C12A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C16 C15 C7 111.9(7) . . ? C16 C15 C17 108.8(7) . . ? C7 C15 C17 110.2(7) . . ? C16 C15 H15 108.6 . . ? C7 C15 H15 108.6 . . ? C17 C15 H15 108.6 . . ? C16A C15A C17A 111.1(7) . . ? C16A C15A C7A 112.4(7) . . ? C17A C15A C7A 110.1(6) . . ? C16A C15A H15B 107.7 . . ? C17A C15A H15B 107.7 . . ? C7A C15A H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C19 C18 C24 129.6(8) . . ? C19 C18 C2 115.2(8) . . ? C24 C18 C2 115.1(7) . . ? C18 C19 C20 132.4(10) . . ? C18 C19 H19 113.8 . . ? C20 C19 H19 113.8 . . ? C22 C20 C19 109.0(9) . . ? C22 C20 C21 111.4(10) . . ? C19 C20 C21 107.4(9) . . ? C22 C20 C23 112.4(8) . . ? C19 C20 C23 108.8(9) . . ? C21 C20 C23 107.6(9) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C22 H22D 109.5 . . ? H22A C22 H22D 141.1 . . ? H22B C22 H22D 56.2 . . ? H22C C22 H22D 56.2 . . ? C20 C22 H22E 109.5 . . ? H22A C22 H22E 56.2 . . ? H22B C22 H22E 141.0 . . ? H22C C22 H22E 56.2 . . ? H22D C22 H22E 109.5 . . ? C20 C22 H22F 109.5 . . ? H22A C22 H22F 56.3 . . ? H22B C22 H22F 56.3 . . ? H22C C22 H22F 141.1 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C18 C24 H24A 109.5 . . ? C18 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C18 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C24 H24D 109.5 . . ? H24A C24 H24D 141.1 . . ? H24B C24 H24D 56.2 . . ? H24C C24 H24D 56.3 . . ? C18 C24 H24E 109.5 . . ? H24A C24 H24E 56.2 . . ? H24B C24 H24E 141.1 . . ? H24C C24 H24E 56.3 . . ? H24D C24 H24E 109.5 . . ? C18 C24 H24F 109.5 . . ? H24A C24 H24F 56.3 . . ? H24B C24 H24F 56.3 . . ? H24C C24 H24F 141.1 . . ? H24D C24 H24F 109.5 . . ? H24E C24 H24F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 N3 0.2(8) . . . . ? C6 N1 C2 N3 167.2(7) . . . . ? C5 N1 C2 C18 176.4(7) . . . . ? C6 N1 C2 C18 -16.6(12) . . . . ? C4 N3 C2 N1 -1.5(8) . . . . ? C6A N3 C2 N1 -174.3(7) . . . . ? C4 N3 C2 C18 -177.6(7) . . . . ? C6A N3 C2 C18 9.5(12) . . . . ? C2 N3 C4 C5 2.2(8) . . . . ? C6A N3 C4 C5 175.5(7) . . . . ? N3 C4 C5 N1 -2.0(8) . . . . ? C2 N1 C5 C4 1.1(8) . . . . ? C6 N1 C5 C4 -166.4(7) . . . . ? C2 N1 C6 C7 -75.0(10) . . . . ? C5 N1 C6 C7 90.2(9) . . . . ? C2 N1 C6 C11 105.4(9) . . . . ? C5 N1 C6 C11 -89.4(9) . . . . ? C2 N3 C6A C11A -81.3(9) . . . . ? C4 N3 C6A C11A 106.8(8) . . . . ? C2 N3 C6A C7A 99.3(9) . . . . ? C4 N3 C6A C7A -72.6(8) . . . . ? C11 C6 C7 C8 0.6(12) . . . . ? N1 C6 C7 C8 -179.0(7) . . . . ? C11 C6 C7 C15 177.4(7) . . . . ? N1 C6 C7 C15 -2.2(11) . . . . ? C11A C6A C7A C8A -1.9(11) . . . . ? N3 C6A C7A C8A 177.4(6) . . . . ? C11A C6A C7A C15A 178.9(7) . . . . ? N3 C6A C7A C15A -1.7(10) . . . . ? C6 C7 C8 C9 -1.4(12) . . . . ? C15 C7 C8 C9 -178.2(7) . . . . ? C6A C7A C8A C9A 2.6(11) . . . . ? C15A C7A C8A C9A -178.3(7) . . . . ? C7 C8 C9 C10 2.0(12) . . . . ? C7A C8A C9A C10A -2.6(12) . . . . ? C8 C9 C10 C11 -1.6(12) . . . . ? C8A C9A C10A C11A 1.7(12) . . . . ? C7 C6 C11 C10 -0.3(12) . . . . ? N1 C6 C11 C10 179.4(7) . . . . ? C7 C6 C11 C12 179.5(8) . . . . ? N1 C6 C11 C12 -0.9(12) . . . . ? C9 C10 C11 C6 0.7(11) . . . . ? C9 C10 C11 C12 -179.1(7) . . . . ? C7A C6A C11A C10A 1.1(11) . . . . ? N3 C6A C11A C10A -178.3(6) . . . . ? C7A C6A C11A C12A -178.8(7) . . . . ? N3 C6A C11A C12A 1.8(11) . . . . ? C9A C10A C11A C6A -0.9(11) . . . . ? C9A C10A C11A C12A 179.0(7) . . . . ? C6 C11 C12 C13 -142.4(8) . . . . ? C10 C11 C12 C13 37.4(11) . . . . ? C6 C11 C12 C14 95.9(9) . . . . ? C10 C11 C12 C14 -84.3(9) . . . . ? C6A C11A C12A C14A 114.8(9) . . . . ? C10A C11A C12A C14A -65.2(9) . . . . ? C6A C11A C12A C13A -122.1(8) . . . . ? C10A C11A C12A C13A 57.9(9) . . . . ? C6 C7 C15 C16 -90.5(9) . . . . ? C8 C7 C15 C16 86.2(9) . . . . ? C6 C7 C15 C17 148.4(8) . . . . ? C8 C7 C15 C17 -35.0(11) . . . . ? C8A C7A C15A C16A 53.0(10) . . . . ? C6A C7A C15A C16A -127.9(8) . . . . ? C8A C7A C15A C17A -71.4(9) . . . . ? C6A C7A C15A C17A 107.7(9) . . . . ? N1 C2 C18 C19 125.8(8) . . . . ? N3 C2 C18 C19 -58.8(10) . . . . ? N1 C2 C18 C24 -51.8(10) . . . . ? N3 C2 C18 C24 123.7(8) . . . . ? C24 C18 C19 C20 -8.2(15) . . . . ? C2 C18 C19 C20 174.7(8) . . . . ? C18 C19 C20 C22 0.1(14) . . . . ? C18 C19 C20 C21 -120.8(11) . . . . ? C18 C19 C20 C23 123.0(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.470 _refine_diff_density_min -1.207 _refine_diff_density_rms 0.105 # Attachment '16.cif' data_16 _database_code_depnum_ccdc_archive 'CCDC 751978' #TrackingRef '16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H53 N2, BR' _chemical_formula_sum 'C43 H53 Br N2' _chemical_formula_weight 677.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.5466(18) _cell_length_b 16.0087(16) _cell_length_c 20.286(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.613(8) _cell_angle_gamma 90.00 _cell_volume 3691.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9022 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.145 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9022 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.1625 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6004 _reflns_number_gt 2841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6004 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1496 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7854(4) 0.26059(19) 0.2685(2) 0.0249(10) Uani 1 1 d . . . N3 N 0.8338(4) 0.32110(19) 0.3816(2) 0.0224(10) Uani 1 1 d . . . C2 C 0.7513(5) 0.2734(2) 0.3165(3) 0.0257(13) Uani 1 1 d . . . C4 C 0.9208(4) 0.3381(2) 0.3748(3) 0.0261(12) Uani 1 1 d . . . H4 H 0.9898 0.3703 0.4132 0.031 Uiso 1 1 calc R . . C5 C 0.8911(5) 0.3015(3) 0.3050(3) 0.0295(13) Uani 1 1 d . . . H5 H 0.9342 0.3031 0.2842 0.035 Uiso 1 1 calc R . . C6 C 0.7245(4) 0.2099(2) 0.1930(3) 0.0234(12) Uani 1 1 d . . . C6A C 0.8548(4) 0.3377(2) 0.4616(3) 0.0250(12) Uani 1 1 d . . . C7 C 0.7316(5) 0.1229(2) 0.2026(3) 0.0277(13) Uani 1 1 d . . . C7A C 0.9233(4) 0.2797(2) 0.5263(3) 0.0246(12) Uani 1 1 d . . . C8 C 0.6703(5) 0.0750(3) 0.1287(3) 0.0318(13) Uani 1 1 d . . . H8 H 0.6726 0.0158 0.1321 0.038 Uiso 1 1 calc R . . C8A C 0.9448(4) 0.2960(3) 0.6025(3) 0.0283(13) Uani 1 1 d . . . H8B H 0.9888 0.2572 0.6477 0.034 Uiso 1 1 calc R . . C9 C 0.6076(5) 0.1130(3) 0.0525(3) 0.0398(15) Uani 1 1 d . . . H9 H 0.5646 0.0794 0.0031 0.048 Uiso 1 1 calc R . . C9A C 0.9026(5) 0.3681(3) 0.6128(3) 0.0333(13) Uani 1 1 d . . . H9B H 0.9173 0.3780 0.6648 0.040 Uiso 1 1 calc R . . C10 C 0.6037(5) 0.1985(3) 0.0438(3) 0.0350(14) Uani 1 1 d . . . H10 H 0.5593 0.2228 -0.0108 0.042 Uiso 1 1 calc R . . C10A C 0.8396(5) 0.4256(3) 0.5488(3) 0.0325(13) Uani 1 1 d . . . H10B H 0.8136 0.4755 0.5579 0.039 Uiso 1 1 calc R . . C11 C 0.6653(5) 0.2496(3) 0.1155(3) 0.0299(13) Uani 1 1 d . . . C11A C 0.8132(4) 0.4120(2) 0.4708(3) 0.0273(13) Uani 1 1 d . . . C12 C 0.6657(5) 0.3442(3) 0.1075(3) 0.0349(14) Uani 1 1 d . . . H12 H 0.6903 0.3696 0.1614 0.042 Uiso 1 1 calc R . . C12A C 0.7409(4) 0.4760(2) 0.4001(3) 0.0291(13) Uani 1 1 d . . . H12B H 0.7228 0.4519 0.3476 0.035 Uiso 1 1 calc R . . C13 C 0.5456(5) 0.3791(3) 0.0359(3) 0.0428(15) Uani 1 1 d . . . H13A H 0.5218 0.3578 -0.0180 0.064 Uiso 1 1 calc R . . H13B H 0.5495 0.4402 0.0363 0.064 Uiso 1 1 calc R . . H13C H 0.4879 0.3618 0.0433 0.064 Uiso 1 1 calc R . . C13A C 0.8118(5) 0.5570(2) 0.4214(3) 0.0398(14) Uani 1 1 d . . . H13D H 0.8319 0.5812 0.4733 0.060 Uiso 1 1 calc R . . H13E H 0.7644 0.5970 0.3750 0.060 Uiso 1 1 calc R . . H13F H 0.8841 0.5444 0.4295 0.060 Uiso 1 1 calc R . . C14 C 0.7576(5) 0.3685(3) 0.0960(3) 0.0404(14) Uani 1 1 d . . . H14A H 0.7385 0.3408 0.0457 0.061 Uiso 1 1 calc R . . H14B H 0.8360 0.3509 0.1457 0.061 Uiso 1 1 calc R . . H14C H 0.7568 0.4292 0.0892 0.061 Uiso 1 1 calc R . . C14A C 0.6248(4) 0.4958(3) 0.3822(3) 0.0367(14) Uani 1 1 d . . . H14D H 0.5815 0.4438 0.3708 0.055 Uiso 1 1 calc R . . H14E H 0.5777 0.5327 0.3331 0.055 Uiso 1 1 calc R . . H14F H 0.6405 0.5236 0.4314 0.055 Uiso 1 1 calc R . . C15 C 0.8086(4) 0.0809(2) 0.2882(3) 0.0268(13) Uani 1 1 d . . . H15 H 0.8197 0.1213 0.3302 0.032 Uiso 1 1 calc R . . C15A C 0.9783(5) 0.2022(2) 0.5189(3) 0.0289(13) Uani 1 1 d . . . H15B H 0.9594 0.2037 0.4623 0.035 Uiso 1 1 calc R . . C16 C 0.7531(4) 0.0014(3) 0.2923(3) 0.0368(14) Uani 1 1 d . . . H16A H 0.6747 0.0145 0.2745 0.055 Uiso 1 1 calc R . . H16B H 0.8027 -0.0199 0.3503 0.055 Uiso 1 1 calc R . . H16C H 0.7464 -0.0411 0.2547 0.055 Uiso 1 1 calc R . . C16A C 0.9287(5) 0.1213(2) 0.5249(4) 0.0453(16) Uani 1 1 d . . . H16D H 0.9636 0.0736 0.5173 0.068 Uiso 1 1 calc R . . H16E H 0.8431 0.1204 0.4807 0.068 Uiso 1 1 calc R . . H16F H 0.9475 0.1177 0.5804 0.068 Uiso 1 1 calc R . . C17 C 0.9302(5) 0.0621(3) 0.3138(3) 0.0346(14) Uani 1 1 d . . . H17A H 0.9227 0.0205 0.2753 0.052 Uiso 1 1 calc R . . H17B H 0.9815 0.0403 0.3716 0.052 Uiso 1 1 calc R . . H17C H 0.9641 0.1135 0.3110 0.052 Uiso 1 1 calc R . . C17A C 1.1106(5) 0.2041(3) 0.5853(4) 0.0442(15) Uani 1 1 d . . . H17D H 1.1415 0.2554 0.5791 0.066 Uiso 1 1 calc R . . H17E H 1.1448 0.1555 0.5783 0.066 Uiso 1 1 calc R . . H17F H 1.1315 0.2028 0.6415 0.066 Uiso 1 1 calc R . . C18 C 0.6375(5) 0.2394(3) 0.2937(3) 0.0390(15) Uani 1 1 d . . . H18 H 0.6411 0.1785 0.2846 0.047 Uiso 1 1 calc R . . C19 C 0.5300(4) 0.2691(3) 0.2088(3) 0.0255(13) Uani 1 1 d . . . C20 C 0.4655(5) 0.2140(3) 0.1414(3) 0.0293(13) Uani 1 1 d . . . H20 H 0.4924 0.1582 0.1488 0.035 Uiso 1 1 calc R . . C21 C 0.3637(5) 0.2377(3) 0.0639(3) 0.0327(14) Uani 1 1 d . . . H21 H 0.3226 0.1980 0.0194 0.039 Uiso 1 1 calc R . . C22 C 0.3207(5) 0.3180(3) 0.0499(3) 0.0340(14) Uani 1 1 d . . . C23 C 0.3841(5) 0.3733(3) 0.1180(4) 0.0362(14) Uani 1 1 d . . . H23 H 0.3558 0.4288 0.1105 0.043 Uiso 1 1 calc R . . C24 C 0.4857(5) 0.3505(3) 0.1951(3) 0.0324(13) Uani 1 1 d . . . H24 H 0.5265 0.3902 0.2396 0.039 Uiso 1 1 calc R . . C25 C 0.2128(5) 0.3449(3) -0.0341(4) 0.0546(17) Uani 1 1 d . . . H25A H 0.2059 0.3133 -0.0785 0.082 Uiso 1 1 calc R . . H25B H 0.2180 0.4047 -0.0418 0.082 Uiso 1 1 calc R . . H25C H 0.1436 0.3344 -0.0376 0.082 Uiso 1 1 calc R . . C26 C 0.6252(5) 0.2406(4) 0.3617(4) 0.0594(18) Uani 1 1 d . . . H26A H 0.6211 0.2992 0.3753 0.071 Uiso 1 1 calc R . . H26B H 0.6955 0.2145 0.4133 0.071 Uiso 1 1 calc R . . C27 C 0.5137(5) 0.1932(3) 0.3348(3) 0.0410(15) Uani 1 1 d . . . C28 C 0.4188(6) 0.2357(3) 0.3168(3) 0.0413(15) Uani 1 1 d . . . H28 H 0.4193 0.2950 0.3153 0.050 Uiso 1 1 calc R . . C29 C 0.3245(5) 0.1972(3) 0.3012(3) 0.0370(14) Uani 1 1 d . . . H29 H 0.2623 0.2294 0.2916 0.044 Uiso 1 1 calc R . . C30 C 0.3181(5) 0.1104(3) 0.2991(3) 0.0348(14) Uani 1 1 d . . . C31 C 0.4113(5) 0.0659(3) 0.3156(3) 0.0384(15) Uani 1 1 d . . . H31 H 0.4089 0.0066 0.3150 0.046 Uiso 1 1 calc R . . C32 C 0.5083(5) 0.1059(3) 0.3330(3) 0.0407(15) Uani 1 1 d . . . H32 H 0.5715 0.0741 0.3437 0.049 Uiso 1 1 calc R . . C33 C 0.2107(6) 0.0667(3) 0.2775(4) 0.069(2) Uani 1 1 d . . . H33A H 0.1613 0.0482 0.2186 0.104 Uiso 1 1 calc R . . H33B H 0.1661 0.1052 0.2855 0.104 Uiso 1 1 calc R . . H33C H 0.2350 0.0181 0.3145 0.104 Uiso 1 1 calc R . . Br1 Br 0.13439(6) 0.35779(3) 0.31787(4) 0.0565(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.034(3) 0.0195(19) 0.023(3) 0.0044(17) 0.018(3) 0.0033(19) N3 0.025(3) 0.0184(19) 0.019(3) 0.0001(17) 0.011(3) -0.0013(18) C2 0.029(4) 0.023(3) 0.026(3) 0.004(2) 0.018(4) 0.005(2) C4 0.021(4) 0.022(2) 0.028(3) -0.001(2) 0.012(3) -0.007(2) C5 0.033(4) 0.029(3) 0.031(3) 0.005(2) 0.023(4) 0.001(2) C6 0.028(4) 0.027(2) 0.021(3) 0.000(2) 0.018(3) 0.003(2) C6A 0.030(4) 0.026(2) 0.017(3) -0.002(2) 0.014(3) -0.003(2) C7 0.036(4) 0.027(3) 0.026(3) 0.003(2) 0.023(4) 0.006(2) C7A 0.021(4) 0.027(3) 0.023(3) -0.003(2) 0.012(3) -0.001(2) C8 0.042(4) 0.028(3) 0.026(3) 0.003(2) 0.022(4) 0.003(2) C8A 0.025(4) 0.034(3) 0.019(3) 0.007(2) 0.010(3) 0.006(2) C9 0.053(5) 0.040(3) 0.028(3) -0.014(3) 0.025(4) -0.011(3) C9A 0.037(4) 0.036(3) 0.026(3) -0.003(2) 0.019(4) 0.001(3) C10 0.042(4) 0.042(3) 0.021(3) 0.005(3) 0.020(4) 0.009(3) C10A 0.037(4) 0.029(3) 0.032(3) -0.010(2) 0.022(4) -0.002(2) C11 0.036(4) 0.036(3) 0.024(3) 0.004(2) 0.022(4) 0.005(2) C11A 0.025(4) 0.024(3) 0.025(3) -0.002(2) 0.011(3) -0.005(2) C12 0.053(5) 0.035(3) 0.030(3) 0.008(2) 0.032(4) 0.009(3) C12A 0.036(4) 0.018(2) 0.030(3) -0.001(2) 0.019(4) 0.002(2) C13 0.047(5) 0.050(3) 0.036(4) 0.013(3) 0.029(4) 0.010(3) C13A 0.039(5) 0.032(3) 0.034(4) -0.001(2) 0.016(4) -0.002(2) C14 0.045(5) 0.038(3) 0.041(4) 0.014(2) 0.028(4) 0.008(3) C14A 0.038(4) 0.031(3) 0.032(4) -0.003(2) 0.018(4) 0.002(2) C15 0.028(4) 0.025(2) 0.022(3) 0.004(2) 0.012(3) 0.003(2) C15A 0.028(4) 0.027(3) 0.026(3) 0.002(2) 0.014(4) 0.007(2) C16 0.037(4) 0.032(3) 0.034(4) 0.009(2) 0.018(4) 0.005(2) C16A 0.054(5) 0.026(3) 0.070(5) 0.000(3) 0.046(4) 0.006(3) C17 0.035(4) 0.028(3) 0.034(4) 0.004(2) 0.018(4) -0.001(2) C17A 0.038(5) 0.038(3) 0.049(4) 0.001(3) 0.023(4) 0.010(3) C18 0.037(5) 0.053(3) 0.025(4) 0.001(3) 0.019(4) -0.003(3) C19 0.024(4) 0.034(3) 0.018(3) -0.001(2) 0.013(4) -0.007(2) C20 0.026(4) 0.031(3) 0.023(3) 0.002(3) 0.012(4) -0.003(3) C21 0.027(5) 0.040(3) 0.023(4) -0.005(3) 0.011(4) -0.013(3) C22 0.027(5) 0.041(3) 0.033(4) 0.009(3) 0.018(4) 0.001(3) C23 0.038(5) 0.035(3) 0.037(4) 0.001(3) 0.024(4) 0.004(3) C24 0.034(5) 0.038(3) 0.027(3) -0.011(3) 0.020(4) -0.011(3) C25 0.045(5) 0.069(4) 0.037(4) 0.015(3) 0.020(5) 0.005(3) C26 0.044(5) 0.087(4) 0.042(4) 0.013(3) 0.024(5) -0.008(3) C27 0.029(5) 0.064(4) 0.019(3) 0.009(3) 0.009(4) -0.012(3) C28 0.050(5) 0.034(3) 0.026(4) 0.007(2) 0.017(4) 0.003(3) C29 0.039(5) 0.042(3) 0.029(4) 0.008(3) 0.021(4) 0.010(3) C30 0.029(4) 0.048(3) 0.022(3) 0.002(3) 0.013(4) -0.006(3) C31 0.057(5) 0.029(3) 0.036(4) -0.007(2) 0.032(4) -0.005(3) C32 0.042(5) 0.054(3) 0.036(4) 0.009(3) 0.029(4) 0.014(3) C33 0.060(6) 0.093(5) 0.059(5) 0.007(4) 0.039(5) -0.019(4) Br1 0.0596(5) 0.0472(3) 0.0837(5) 0.0205(3) 0.0551(5) 0.0097(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.356(5) . ? N1 C5 1.386(6) . ? N1 C6 1.447(5) . ? N3 C2 1.338(6) . ? N3 C4 1.384(5) . ? N3 C6A 1.475(5) . ? C2 C18 1.515(6) . ? C4 C5 1.331(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C11 1.390(6) . ? C6 C7 1.402(5) . ? C6A C7A 1.397(6) . ? C6A C11A 1.398(5) . ? C7 C8 1.400(6) . ? C7 C15 1.514(6) . ? C7A C8A 1.397(5) . ? C7A C15A 1.533(5) . ? C8 C9 1.354(6) . ? C8 H8 0.9500 . ? C8A C9A 1.384(5) . ? C8A H8B 0.9500 . ? C9 C10 1.377(6) . ? C9 H9 0.9500 . ? C9A C10A 1.373(6) . ? C9A H9B 0.9500 . ? C10 C11 1.400(6) . ? C10 H10 0.9500 . ? C10A C11A 1.393(6) . ? C10A H10B 0.9500 . ? C11 C12 1.523(5) . ? C11A C12A 1.528(6) . ? C12 C13 1.518(7) . ? C12 C14 1.544(5) . ? C12 H12 1.0000 . ? C12A C14A 1.524(6) . ? C12A C13A 1.540(6) . ? C12A H12B 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C15 C17 1.529(6) . ? C15 C16 1.537(5) . ? C15 H15 1.0000 . ? C15A C17A 1.512(7) . ? C15A C16A 1.524(5) . ? C15A H15B 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17A H17D 0.9800 . ? C17A H17E 0.9800 . ? C17A H17F 0.9800 . ? C18 C26 1.497(6) . ? C18 C19 1.508(7) . ? C18 H18 1.0000 . ? C19 C20 1.389(6) . ? C19 C24 1.402(6) . ? C20 C21 1.379(6) . ? C20 H20 0.9500 . ? C21 C22 1.380(6) . ? C21 H21 0.9500 . ? C22 C23 1.397(7) . ? C22 C25 1.489(7) . ? C23 C24 1.371(7) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.549(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.369(7) . ? C27 C32 1.399(6) . ? C28 C29 1.348(6) . ? C28 H28 0.9500 . ? C29 C30 1.393(6) . ? C29 H29 0.9500 . ? C30 C31 1.375(6) . ? C30 C33 1.506(7) . ? C31 C32 1.379(6) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.0(4) . . ? C2 N1 C6 126.0(4) . . ? C5 N1 C6 124.9(3) . . ? C2 N3 C4 109.1(3) . . ? C2 N3 C6A 129.1(4) . . ? C4 N3 C6A 120.0(4) . . ? N3 C2 N1 106.9(4) . . ? N3 C2 C18 129.9(4) . . ? N1 C2 C18 123.1(5) . . ? C5 C4 N3 108.0(4) . . ? C5 C4 H4 126.0 . . ? N3 C4 H4 126.0 . . ? C4 C5 N1 107.0(4) . . ? C4 C5 H5 126.5 . . ? N1 C5 H5 126.5 . . ? C11 C6 C7 123.5(4) . . ? C11 C6 N1 118.6(4) . . ? C7 C6 N1 117.8(4) . . ? C7A C6A C11A 123.6(4) . . ? C7A C6A N3 116.8(3) . . ? C11A C6A N3 119.4(4) . . ? C8 C7 C6 116.9(4) . . ? C8 C7 C15 120.4(4) . . ? C6 C7 C15 122.6(4) . . ? C6A C7A C8A 116.9(4) . . ? C6A C7A C15A 123.7(4) . . ? C8A C7A C15A 119.3(4) . . ? C9 C8 C7 120.2(4) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C9A C8A C7A 120.6(4) . . ? C9A C8A H8B 119.7 . . ? C7A C8A H8B 119.7 . . ? C8 C9 C10 122.5(4) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C10A C9A C8A 120.9(4) . . ? C10A C9A H9B 119.6 . . ? C8A C9A H9B 119.6 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C9A C10A C11A 121.2(4) . . ? C9A C10A H10B 119.4 . . ? C11A C10A H10B 119.4 . . ? C6 C11 C10 116.8(4) . . ? C6 C11 C12 122.3(4) . . ? C10 C11 C12 120.8(4) . . ? C10A C11A C6A 116.8(4) . . ? C10A C11A C12A 120.1(4) . . ? C6A C11A C12A 123.1(4) . . ? C13 C12 C11 112.9(4) . . ? C13 C12 C14 110.6(3) . . ? C11 C12 C14 109.1(3) . . ? C13 C12 H12 108.0 . . ? C11 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C14A C12A C11A 111.9(3) . . ? C14A C12A C13A 109.9(3) . . ? C11A C12A C13A 110.7(4) . . ? C14A C12A H12B 108.1 . . ? C11A C12A H12B 108.1 . . ? C13A C12A H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12A C14A H14D 109.5 . . ? C12A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C12A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C7 C15 C17 110.4(3) . . ? C7 C15 C16 113.0(4) . . ? C17 C15 C16 110.7(3) . . ? C7 C15 H15 107.5 . . ? C17 C15 H15 107.5 . . ? C16 C15 H15 107.5 . . ? C17A C15A C16A 110.5(4) . . ? C17A C15A C7A 110.4(4) . . ? C16A C15A C7A 112.2(4) . . ? C17A C15A H15B 107.9 . . ? C16A C15A H15B 107.9 . . ? C7A C15A H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C26 C18 C19 114.5(4) . . ? C26 C18 C2 116.8(5) . . ? C19 C18 C2 113.0(4) . . ? C26 C18 H18 103.5 . . ? C19 C18 H18 103.5 . . ? C2 C18 H18 103.5 . . ? C20 C19 C24 116.7(5) . . ? C20 C19 C18 120.4(4) . . ? C24 C19 C18 122.7(4) . . ? C21 C20 C19 122.2(4) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 121.1(5) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C23 116.9(5) . . ? C21 C22 C25 121.6(5) . . ? C23 C22 C25 121.5(5) . . ? C24 C23 C22 122.3(5) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C19 120.6(4) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C26 C27 111.7(5) . . ? C18 C26 H26A 109.3 . . ? C27 C26 H26A 109.3 . . ? C18 C26 H26B 109.3 . . ? C27 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C32 117.3(5) . . ? C28 C27 C26 120.7(5) . . ? C32 C27 C26 121.8(5) . . ? C29 C28 C27 122.9(5) . . ? C29 C28 H28 118.5 . . ? C27 C28 H28 118.5 . . ? C28 C29 C30 120.2(5) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 118.2(5) . . ? C31 C30 C33 121.1(5) . . ? C29 C30 C33 120.7(5) . . ? C30 C31 C32 121.2(4) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C31 C32 C27 120.1(5) . . ? C31 C32 H32 119.9 . . ? C27 C32 H32 119.9 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 N1 -0.3(5) . . . . ? C6A N3 C2 N1 -164.7(4) . . . . ? C4 N3 C2 C18 -178.5(4) . . . . ? C6A N3 C2 C18 17.1(8) . . . . ? C5 N1 C2 N3 -0.1(5) . . . . ? C6 N1 C2 N3 177.7(4) . . . . ? C5 N1 C2 C18 178.3(4) . . . . ? C6 N1 C2 C18 -3.9(6) . . . . ? C2 N3 C4 C5 0.6(5) . . . . ? C6A N3 C4 C5 166.7(4) . . . . ? N3 C4 C5 N1 -0.6(5) . . . . ? C2 N1 C5 C4 0.5(5) . . . . ? C6 N1 C5 C4 -177.3(4) . . . . ? C2 N1 C6 C11 107.8(5) . . . . ? C5 N1 C6 C11 -74.8(6) . . . . ? C2 N1 C6 C7 -74.1(6) . . . . ? C5 N1 C6 C7 103.3(5) . . . . ? C2 N3 C6A C7A 84.9(6) . . . . ? C4 N3 C6A C7A -78.0(5) . . . . ? C2 N3 C6A C11A -99.5(5) . . . . ? C4 N3 C6A C11A 97.6(5) . . . . ? C11 C6 C7 C8 -3.2(7) . . . . ? N1 C6 C7 C8 178.8(4) . . . . ? C11 C6 C7 C15 172.4(4) . . . . ? N1 C6 C7 C15 -5.7(6) . . . . ? C11A C6A C7A C8A 3.6(7) . . . . ? N3 C6A C7A C8A 179.0(4) . . . . ? C11A C6A C7A C15A -174.3(4) . . . . ? N3 C6A C7A C15A 1.2(7) . . . . ? C6 C7 C8 C9 -0.1(7) . . . . ? C15 C7 C8 C9 -175.8(4) . . . . ? C6A C7A C8A C9A -2.1(7) . . . . ? C15A C7A C8A C9A 175.9(4) . . . . ? C7 C8 C9 C10 2.0(8) . . . . ? C7A C8A C9A C10A -0.6(7) . . . . ? C8 C9 C10 C11 -0.6(8) . . . . ? C8A C9A C10A C11A 2.0(8) . . . . ? C7 C6 C11 C10 4.4(7) . . . . ? N1 C6 C11 C10 -177.6(4) . . . . ? C7 C6 C11 C12 -176.0(4) . . . . ? N1 C6 C11 C12 2.0(7) . . . . ? C9 C10 C11 C6 -2.5(7) . . . . ? C9 C10 C11 C12 177.9(4) . . . . ? C9A C10A C11A C6A -0.6(7) . . . . ? C9A C10A C11A C12A 178.7(4) . . . . ? C7A C6A C11A C10A -2.3(7) . . . . ? N3 C6A C11A C10A -177.6(4) . . . . ? C7A C6A C11A C12A 178.4(4) . . . . ? N3 C6A C11A C12A 3.1(7) . . . . ? C6 C11 C12 C13 -137.4(5) . . . . ? C10 C11 C12 C13 42.2(6) . . . . ? C6 C11 C12 C14 99.2(5) . . . . ? C10 C11 C12 C14 -81.2(6) . . . . ? C10A C11A C12A C14A -54.0(6) . . . . ? C6A C11A C12A C14A 125.3(4) . . . . ? C10A C11A C12A C13A 69.0(5) . . . . ? C6A C11A C12A C13A -111.8(5) . . . . ? C8 C7 C15 C17 83.6(5) . . . . ? C6 C7 C15 C17 -91.8(5) . . . . ? C8 C7 C15 C16 -41.1(6) . . . . ? C6 C7 C15 C16 143.6(4) . . . . ? C6A C7A C15A C17A 120.5(5) . . . . ? C8A C7A C15A C17A -57.3(5) . . . . ? C6A C7A C15A C16A -115.8(5) . . . . ? C8A C7A C15A C16A 66.3(6) . . . . ? N3 C2 C18 C26 -16.4(7) . . . . ? N1 C2 C18 C26 165.7(4) . . . . ? N3 C2 C18 C19 119.5(5) . . . . ? N1 C2 C18 C19 -58.4(5) . . . . ? C26 C18 C19 C20 -113.3(5) . . . . ? C2 C18 C19 C20 109.7(5) . . . . ? C26 C18 C19 C24 62.3(6) . . . . ? C2 C18 C19 C24 -74.7(5) . . . . ? C24 C19 C20 C21 1.0(6) . . . . ? C18 C19 C20 C21 176.9(4) . . . . ? C19 C20 C21 C22 -0.3(6) . . . . ? C20 C21 C22 C23 -0.8(6) . . . . ? C20 C21 C22 C25 178.2(4) . . . . ? C21 C22 C23 C24 1.1(6) . . . . ? C25 C22 C23 C24 -177.8(4) . . . . ? C22 C23 C24 C19 -0.4(7) . . . . ? C20 C19 C24 C23 -0.6(6) . . . . ? C18 C19 C24 C23 -176.4(4) . . . . ? C19 C18 C26 C27 52.7(6) . . . . ? C2 C18 C26 C27 -172.0(4) . . . . ? C18 C26 C27 C28 -108.4(6) . . . . ? C18 C26 C27 C32 75.7(6) . . . . ? C32 C27 C28 C29 2.7(8) . . . . ? C26 C27 C28 C29 -173.3(5) . . . . ? C27 C28 C29 C30 -2.9(8) . . . . ? C28 C29 C30 C31 1.8(7) . . . . ? C28 C29 C30 C33 -177.0(5) . . . . ? C29 C30 C31 C32 -0.7(7) . . . . ? C33 C30 C31 C32 178.1(5) . . . . ? C30 C31 C32 C27 0.6(7) . . . . ? C28 C27 C32 C31 -1.5(7) . . . . ? C26 C27 C32 C31 174.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.745 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.745 _refine_diff_density_max 0.751 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.059